50 Best Bermuda Vacation rentals on Holiday Lettings - Estates

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Southampton Parish
35 properties
Smith's Parish
12 properties
Pembroke Parish
10 properties
St. George's Parish
9 properties
Warwick Parish
8 properties
Sandys Parish
5 properties
Paget Parish
5 properties

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89 Vacation rentals

(4) Excellent 

12

South Shore Vacation apartment rental

Southampton Parish / South Shore

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
A contemporary ocean-front apartment with access to a horizon pool located at the end of a quiet lane on the south shore between West Whale Bay and Church Bay. Ideal for those looking to relax, with panoramic ocean views from every room and a private lawn where you can …see more

from $295 / night

$2065 / week

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from $295 / night

25

Bermuda Vacation home rental

Bermuda / Paget Parish

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Child friendly
Sprawling graciously , in a park like setting, filled with grand old majestic trees, sits this five bedroom five and a half bathroom entertainer's paradise. Behind the enchanting traditional Bermuda façade lies a modern interpretation of sophisticated and care-free urba …see more

from $1277 / night

$8933 - $12506 / week

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from $1277 / night

17

Bermuda Vacation studio rental

Bermuda / Southampton Parish

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Private and cozy studio located on a hill which gives you a breathtaking view of Jews Bay and Dockyard (home of the Americas Cup). The studio is part of a large house with a separate entrance. It is fully furnished - comfortable queen size bed, love seat, dining for 2, …see more

from $150 / night

$1050 / week

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from $150 / night

11

Vacation home in Bermuda

Bermuda / Southampton Parish

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front one and a half bedroom unit is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby cl …see more

from $215 / night

$1505 / week

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from $215 / night

(1) Excellent 

21

Vacation studio with swimming pool, tennis court in Paget Parish

Bermuda / Paget Parish

Studio 2 5 nights min

  • Studio
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
•Consistently rated 5★★★★★ •Your OWN Private Pool & Tennis Court •Walk to Hamilton •5 min. ride to Elbow Beach •High speed Internet •New Pillow-top, king-sized bed •Fully equipped + stocked kitchen •Near bus stops to both ends of the island •42" TV •Extremely safe neigh …see more

from $179 / night

$1253 / week

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from $179 / night

(16) Very Good 

10

Vacation cottage in Bermuda

St. George's Parish / St. George

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Experience your Bermuda vacation in the World Heritage Town of St Georges! This traditional Bermuda cottage has been thoroughly updated and modernized whilst retaining charm and character. Amenities include an en-suite master bedroom with King size bed, a modern fully …see more

from $175 / night

$1250 / week

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from $175 / night

(1) Excellent 

17

Bermuda Vacation studio rental

Sandys Parish / Somerset Village

Studio 3 4 nights min

  • Studio
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Air conditioning
This studio sits in the heart of Somerset Village in Sandys, Bermuda. Easily an ideal place for couples visiting Bermuda without transportation. Its the perfect spot with a restaurant across the street, local shops, beaches, bus stops and entertainment within close prox …see more

from $200 / night

$1400 / week

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Responds fast!
avg. 2 hours 53 minutes

from $200 / night

10

Vacation studio in Southampton Parish

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

10

Vacation studio in Bermuda

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

10

Vacation studio in Southampton Parish

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

(1) Excellent 

9

Vacation home with shared pool in Smith's Parish

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
The pool house is a studio and has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet residential neighborhood. Bus stop is a 3 minute walk, beautiful John Smith's Bay beach is a 5 minute walk and a grocery store is a 10 min …see more

from $120 / night

$770 - $1155 / week

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Responds fast!
avg. 1 hour 20 minutes

from $120 / night

10

Vacation studio in Bermuda

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

12

Vacation home in Bermuda

Bermuda / Southampton Parish

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
This state of the art condominium is nestled in a residential neighborhood in Southampton, and only a stone’s throw away from some of the best snorkeling in Bermuda- Church Bay. With easy access to a main bus route, this location provides all the comforts of home, while …see more

from $400 / night

$2800 / week

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from $400 / night

(4) Excellent 

18

Vacation b&b in St. George

St. George's Parish / St. George

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Aunt Nea's Inn is a historic Bermudian guest house located in the UNESCO World Heritage site of St. George's. From original woodwork and building craftsmanship from the 1700s to stunning harbour and garden views, you will love staying in this very special property in th …see more

from $225 / night

$1575 / week

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from $225 / night

25

Vacation home in Bermuda

Bermuda / Southampton Parish

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Ask about children
  • Air conditioning
Situated on the waters of the Great Sound, this home boasts a private dock and small beach. The minute you walk through the front door your eyes are drawn to the pool, large front yard and expansive views of the Great Sound through a bank of French doors that lead from …see more

from $1551 / night

$10851 / week

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from $1551 / night

(1) Very Good 

16

Vacation apartment in Bermuda

Bermuda / Hamilton Parish

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Attractive lower apartment on a property with panoramic seascape views of North Shore Bermuda. Extra features include excursions to Bermuda Railway trail, fishing off of Bay Island, visits to nearby Crystal Caves (we are descendants of the discoverers) and Grotto Bay Ca …see more

from $70 / night

$490 / week

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Responds fast!
avg. 2 hours 10 minutes

from $70 / night

10

Vacation studio in Bermuda

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

14

Vacation cottage in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Adorable stand alone cottage located in Southampton with stunning views of the Great Sound. The cottage itself consists of two bedrooms, one bathroom, eat-in kitchen, a living room with fireplace, a covered porch and a lower level laundry room. The cottage has two acces …see more

from $202 / night

$1414 / week

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from $202 / night

10

Vacation studio in Bermuda

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

10

Vacation studio in Southampton Parish

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

(10) Excellent 

8

Hamilton Vacation apartment rental

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $200 / night

$1300 / week

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Responds fast!
avg. 3 hours 55 minutes

from $200 / night

25

Vacation home in Bermuda

Bermuda / Southampton Parish

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This lovely waterfront home has stunning views of the Great Sound and consists of 4 bedrooms with 4 bathrooms. The master bed with a king bed, two guest rooms with two twins and the other guest room with a double bed. There is a large formal living room with wood burnin …see more

from $750 / night

$5244 / week

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Responds fast!
avg. 3 hours 13 minutes

from $750 / night

(1) Excellent 

9

Vacation apartment with shared pool in Bermuda

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
The apartment is close to the beautiful John Smiths Bay beach - an 8 minute walk away. The pool is on the property and around the back from the apartment. The apartment has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet …see more

from $120 / night

$770 - $1120 / week

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avg. 1 hour 20 minutes

from $120 / night

14

Vacation cottage with shared pool in Bermuda

St. George's Parish / St. George

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
1 WEEK ONLY!!! TIME SHARE !!!FREE STANDING COTTAGE HOME IN PRIVATE SETTING WITH POOL STEPS AWAY. MASTER SUITE, IS ON 2ND FLR FEATURES SOAK TUB, SHOWER & DOUBLE VANITY.HAS BALCONY WITH VIEWS. 2ND PRIVATE BEDRM ON 1ST FLOOR HAS 2 TWIN BEDS & 2ND FULL BATH. LIVING RM HAS H …see more

from $458 / night

$3200 / week

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from $458 / night

12

Vacation apartment in Bermuda

St. George's Parish / St. George

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Newly renovated accommodation in a large garden setting located in the heart of the old town of St George's includes Continental Breakfast.Close to Ferry and bus routes,local corner store,restaurants and shops. On the property their is use of BBQ with outdoor dining fa …see more

from $125 / night

$875 / week

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from $125 / night

(1) Very Good 

8

Vacation apartment in Bermuda

Pembroke Parish / Hamilton

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Air conditioning
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $210 / night

$1400 / week

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Responds fast!
avg. 3 hours 55 minutes

from $210 / night

(7) Excellent 

17

Vacation home in St. George

St. George's Parish / St. George

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0.5 mi
  • Ask about children
  • Air conditioning
1768 historic Bermuda cottage, restored with modern conveniences, situated in the Town of St George and just walking distance to beautiful beaches and historic forts as well as restaurants and shops. Cottage is set in a landscaped garden with tropical fruit trees and ea …see more

from $195 / night

$1365 / week

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Responds fast!
avg. 38 minutes

from $195 / night

(5) Very Good 

12

Apartment rental in Hamilton Parish

Bermuda / Hamilton Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
'Neston' is on 2 acres of property, located in a very quiet and secluded neighborhood. Enjoy the Beautiful Views of Harrington Sound one of the most Beautiful inlets in Bermuda. Harrington Sound is a wonderful inland lake in Bermuda surrounded mainly by Hamilto …see more

from $195 / night

$1365 / week

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from $195 / night

(6) Excellent 

4

Vacation studio with shared pool in Bermuda

Pembroke Parish / Hamilton

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Hibiscus Hideaway is a self-catered, studio accommodation for tourists and business travelers, located in a serene and very convenient location. A pleasant 5-minute walk into the heart of Hamilton, making all of the amenities easily accessible (shops, restaurants, groce …see more

from $150 / night

$1050 - $1225 / week

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from $150 / night

14

Vacation cottage in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Adorable stand alone cottage located in Southampton with stunning views of the Great Sound. The cottage itself consists of two bedrooms, one bathroom, eat-in kitchen, a living room with fireplace, a covered porch and a lower level laundry room. The cottage has two acces …see more

from $198 / night

$1380 / week

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Responds fast!
avg. 3 hours 13 minutes

from $198 / night

10

Vacation home in Bermuda

Bermuda / Southampton Parish

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
This aptly named home is perched above Bermuda's stunning South Shore in Southampton, with unobstructed ocean views. The construction of the home allows for panaormaic views from most of the house, with porches on the upper level and lower level- also home to a pool. Ha …see more

from $1443 / night

$10101 / week

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Responds fast!
avg. 3 hours 13 minutes

from $1443 / night

(1) Very Good 

4

Vacation apartment in St. George

St. George's Parish / St. George

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
A Historic, elegant family home in a quiet neighbourhood within a 5 minute walk to the town centre and bus stops. St. George's harbour (alongside the town centre) is the site for the new marina coming in 2016 and currently has facilities for visiting yachts. Closest bea …see more

from $165 / night

$1155 / week

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from $165 / night

6

Apartment rental in Hamilton

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $235 / night

$1500 / week

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Responds fast!
avg. 3 hours 55 minutes

from $235 / night

(9) Excellent 

12

Vacation apartment in Bermuda

Bermuda / Pembroke Parish

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
It really isn't too late to come and experience the hidden gem of Bermuda and live like the locals do in a safe, family-like neighbourhood. Located on the north side of Bermuda amongst two spectacular parks, with caves that you can explore right at your finger tips. Cen …see more

from $135 / night

$945 / week

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Responds fast!
avg. 1 hour 41 minutes

from $135 / night

11

Vacation home in Southampton Parish

Bermuda / Southampton Parish

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front one and a half bedroom unit is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby cl …see more

from $339 / night

$2373 / week

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Responds fast!
avg. 3 hours 13 minutes

from $339 / night

10

Vacation studio in Southampton Parish

Bermuda / Southampton Parish

Studio 4 3 nights min

  • Studio
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Situated between the picturesque Port Royal Golf Course and Bermuda’s famed South Shore, this Ocean front studio is the perfect getaway for the discerning traveler. Only steps from a private beach, there is also a restaurant located in the nearby clubhouse for convenien …see more

from $150 / night

$1050 / week

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from $150 / night

(3) Excellent 

11

Vacation apartment in Warwick Parish

Bermuda / Warwick Parish

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This cute studio is spacious and comes with all the amenities needed to create a home away from home. The main room is 29ft x 16 and it comes with an open space sleeping and living quarters. The separate kitchen consists of a washer/dryer combo, stainless steel gas …see more

from $129 / night

$903 / week

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Responds fast!
avg. 3 hours 4 minutes

from $129 / night

(1) Excellent 

48

Bermuda Vacation home rental

Bermuda / Warwick Parish

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This is a small neighborhood in a great location. Children love that there is a lot of space to run and play. The adults love that they have their own private outdoor area. Ocean Sounds is close to the beaches. It is good for couples, business travelers, families (with …see more

from $500 / night

$7140 - $7840 / week

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Responds fast!
avg. 2 hours 58 minutes

from $500 / night

33

Vacation home in Bermuda

St. George's Parish / St. George

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Beautiful 1,507 sq. ft. vacation rental. Two BR luxury home; kitchen; large DR; relaxing LR with a dinette set, fireplace and a sleeper sofa for two; laundry room; master bedroom with spa bathroom and fireplace; AC/Heating units; four flat screen TVs, two large porches …see more

from $350 / night

$2450 / week

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from $350 / night

(1) Excellent 

7

Vacation apartment in Bermuda

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $245 / night

$1600 / week

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Responds fast!
avg. 3 hours 55 minutes

from $245 / night